2-Acetylpyridine → 5-Chloro-3-hydroxy-3-(2-oxo-2-pyridin-2-ylethyl)-1-propylindol-2-one

HRID 1523068Notes

Reaction equation

HRID 1523068 reaction equation
[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([OH:23])([CH2:14][C:15](=[O:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[C:6]1=[O:24])[CH2:2][CH2:3]C.[Cl:25]C1C=C2C(=CC=1)N(CCC)C(=O)C2=O.C(C1C=CC=CN=1)(=O)C>>[Cl:25][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[N:5]([CH2:1][CH2:2][CH3:3])[C:6](=[O:24])[C:7]2([OH:23])[CH2:14][C:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1

Participants

4

Reactant 3

HCID 142862-AcetylpyridineHCID 29441601-Butyl-3-hydroxy-3-(2-oxo-2-pyridin-2-ylethyl)indol-2-oneHCID 29882815-Chloro-1-propylindoline-2,3-dione

Product 1

HCID 49092155-Chloro-3-hydroxy-3-(2-oxo-2-pyridin-2-ylethyl)-1-propylindol-2-one

Procedure

This compound was made in a similar manner to 1-butyl-3-hydroxy-3-(2-oxo-2-(pyridin-2-yl)ethyl)indolin-2-one using 5-chloro-1-propylindoline-2,3-dione and 2-acetyl pyridine (purchased from Fisher Scientific). 1H-NMR δ 8.70 (d, 1H), 8.10 (d, 1H), 7.92 (t, 1H), 7.56 (dd, 1H), 7.28 (m, 2H), 6.79 (d, 1H), 3.63 (m, 5H), 1.70 (m, 2H), 0.96 (t, 3H). Calculated mass for C18H17ClN2O3, 344.09. Observed 345.0 (M+1), 367.1 (M+Na).

Sources & evidence

ORD record
ord-29668913828145f8a9d16d42296ec4fe
Source dataset
uspto-grants-2015_07
Patent number
US09079853B2

Reaction notes

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